Dates With Sean Penn, A Night With Tupac & The TRUTH About Her Divorce -- Jewel Reveals Secrets Of Her Rags-To-Riches Life In Her Shocking New Memoir

Jewel was the music world's '90s folk darling with her adorably crooked teeth and a squeaky-clean reputation. Little did fans realize her life was jam-packed with Hollywood drama! In her new memoir, Never Broken: Songs Are Only Half the Story, the native Alaskan, now a 41-year-old single mom, tells all.

In 1995, the budding singer began to date much older L.A. bad boy Sean Penn after he saw her perform on TV. He called her up and asked her to compose a song for an upcoming movie- but the relationship soon grew personal. Jewel, who then wore thrift store clothes, says she felt like "Cinderella going to the ball" when he whisked her away to red carpets in Paris and Venice.

Though he had a womanizer reputation, Jewel insists Penn was a total sweetheart during their relationship, even flying her father in from Alaska to watch her perform as Dorothy in The Wizard of Oz at New York's Lincoln Center.

The romance ended before Jewel ever found true fame. "The breakup was hard for me," she admits.

Momager from hell! Due to her manager mother Nedra's frivolous spending, Jewel says she became millions of dollars in debt at the height of her success. "My mom lived like a rock star," she claims. "She flew in yoga instructors from Hawaii and took jets everywhere."

Jewel stopped speaking with her mother completely in 2003. "I can't tell you the tears I've cried to see who my mom really is," she writes. "I can't tell you about the pain, and how my heart to this day screams to have a mom in my life. But I know that is it not safe with her."

At a party in 1996, Jewel met rapper Tupac. "He was apparently taken with me because he stopped in his tracks and gave me an electric stare that was hard to mistake," she says. He asked her to accompany him and his crew to Las Vegas. The singer shut him down— and he was shot and later died just days later.

Marilyn Manson was another big fan, Jewel claims. He went up to her and said he loved the song "I'm Sensitive." "Not a song choice I expected from a man wearing white contact lenses and plastic pants," she writes.

Shocking fans, Jewel and her husband announced their separation in 2014. "We worked hard on our relationship. But it became evident to me that while we loved each other dearly, we were hurting our love, not building it," she explains in the book. "And we did not want that to be what our son grew up to see."

She calls the split "heartbreaking" and a "loss of a dream." "The shock was staggering," she admits.

But she is trying to move on. "Ty and I are both committed to being great parents and finding our way with love. I am healthy. I have a job that I love," she insists.